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Theoricraftwise, E rank increase AD ratio and the base dama increase is so negligible while getting the increase 11% AS asap would help stack E sooner and faster; since the AP ratio on fix,the base damage only increase by 25 each rank but it scale at 25%AP; and the CDR make it from 16sec to 14 sec in 5 rank, nothing to motivate a rush as 2nd ability max; not to forget that the active of E does physical damage so have no synergy with void staff.
Q max- Q max is best for situations vs mobile or bursty enemy champions, where you have to stack your E before they escape or before they get their damage on you, this is better for a hybrid on hit Tristana, while AP assassin Tristana in the late game will mostly rely on just her W and R to deal the bulk of the damage
E max- E max is best in shorter burstier trades, you want the base damage higher because you're getting your spell rotation off before you can stack all 4 of your bombs which is much more of what we're looking to do as an assassin (certainly you want to weave in auto's) but you won't be relying on W anytime after laning phase
E max also allows you faster waveclear as the passive spell effect scales off AP
As far as tower sieging goes either Q or E max I've found to deal about the same damage to towers regardless of which is maxed first.
and while E does not synergize well with the void staff, the W and R will, which is going to be the bulk of the damage
in the early game you want to get 4 bomb stacks for the sole purpose of resetting W, in late game, you want the bomb at a higher base damage to increase your overall combo damage.